CN108395667A - Crude phenols comprehensive utilization process - Google Patents
Crude phenols comprehensive utilization process Download PDFInfo
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- CN108395667A CN108395667A CN201711375797.3A CN201711375797A CN108395667A CN 108395667 A CN108395667 A CN 108395667A CN 201711375797 A CN201711375797 A CN 201711375797A CN 108395667 A CN108395667 A CN 108395667A
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- Prior art keywords
- crude phenols
- comprehensive utilization
- utilization process
- process according
- phenolic resin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
Abstract
This application involves a kind of coal chemical industry more particularly to a kind of crude phenols comprehensive utilization process；It includes the following steps：Crude phenols and formalin are mixed to form the first mixture by the first step, and aqueous hydrochloric acid solution is added and carries out condensation reaction 1 hour to 2 hours, obtains the mixed aqueous solution of small molecule condensation product；The mixed aqueous solution of above-mentioned small molecule condensation product is carried out polycondensation reaction 3 to 6 hours by second step；Third walks, and is dehydrated above-mentioned resin water mixed liquid to obtain phenolic resin.Due to implementing above-mentioned technical proposal, the application is using crude phenols directly as raw material, it is reacted with formaldehyde and prepares phenolic resin intermediate product, the process is without distilling cutting higher boiling aldehydes matter, low energy consumption, and no waste generates, and avoids environmental pollution, the phenolic resin precast is modulated with catalytic slurry again, prepares better than No. 200 road asphalt series of products.The application technological process is short, and equipment is few, and low energy consumption, and pollution is few, while solving the problems, such as that slurry oil technical indicator does not reach requirement.
Description
Technical field
This application involves a kind of coal chemical industry more particularly to a kind of crude phenols comprehensive utilization process.
Background technology
Crude phenols obtain fraction containing phenol to coal tar distillation and are processed to obtain, can be used for produce synthetic fibers, pesticide,
Engineering plastics and dyestuff intermediate.It is mainly used for extracting phenol, o-cresol, M-and P-cresols, xylenol, 3,5- xylenols etc., is
The important source material of the industries such as the solvent and plastics of premium insulation paint, medicine, mould inhibitor.Since crude phenols form complicated, each component
Between boiling point it is very close, be processed that separating technology is comparatively laborious, and equipment is more to it, capital equipment is：Dehydrating tower, de- slag
Tower, phenol tower, o-cresol tower, industrial cresols tower and xylenol tower；Main technique is continuous dehydration, de- slag, finally produces product
Phenol, o-cresol, industrial cresols and xylenol fraction.Since the process costs of purification ＆ isolation are high, usual crude phenols are as coking
Waste is burnt up, and has larger pollution to environment.
The technology the problem is that：(1) processing separating technology is cumbersome, high energy consumption；(2) phenol Slag treatment difficulty is big, to ring
There is larger pollution in border；(3) processing procedure has a large amount of waste water to generate, and intractability is big.
Invention content
The purpose of the application is to propose that a kind of technological process is short, low energy consumption, pollute less, the crude phenols synthesis that the production output value is high
Utilize technique.
What the application was realized in：Crude phenols comprehensive utilization process comprising following step：The first step, by crude phenols and first
Aldehyde aqueous solution is mixed to form the first mixture, and aqueous hydrochloric acid solution is added and carries out condensation reaction 1 hour to 2 hours, obtains small molecule
The mixed aqueous solution of condensation product；The mixed aqueous solution of above-mentioned small molecule condensation product is carried out polycondensation reaction 3 to 6 hours by second step,
Obtain resin water mixed liquid；Third walks, and is dehydrated above-mentioned resin water mixed liquid to obtain phenolic resin；4th step, by above-mentioned phenolic aldehyde
Resin stirs to get modified pitch with catalytic slurry.
Further, the setting-up point in the first step is 65 DEG C to 75 DEG C, and the polycondensation reaction temperature in second step is
85 DEG C to 95 DEG C, the dehydration temperaturre during third walks is 120 DEG C to 170 DEG C.
Further, the setting-up point in the first step is preferably 70 DEG C, and the polycondensation reaction temperature in second step is preferred
It it is 90 DEG C, the dehydration temperature in third step is preferably 130 DEG C to 135 DEG C.
Further, the condensation reaction pressure in the first step is -0.05MPa to 0.05MPa, the polycondensation reaction in second step
Pressure is -0.05MPa to 0.05MPa, and the dewatering pressure in third step is -0.01MPa to -0.1MPa.
Further, the aqueous hydrochloric acid solution quality being added in the first step is the 0.2% to 5% of the first mixture gross mass,
Aqueous hydrochloric acid solution a concentration of 8% to 12%.
Further, the aqueous hydrochloric acid solution quality being added in the first step accounts for the first mixture gross mass percentage
2%, aqueous hydrochloric acid solution concentration is preferably 10%.
Further, the reaction time of polycondensation reaction is 5 hours in second step.
Further, the molar ratio of the formaldehyde in the crude phenols and formalin in the first step is 1:0.4 to 1:2；It is preferred that
It is 1:0.75.
Further, in the formalin in the first step formaldehyde mass fraction>35%.
Further, in the 4th step phenolic resin and catalytic slurry with mass ratio 3:1 to 9:1, temperature is 95 DEG C to 180
DEG C, it is uniformly mixing to obtain modified pitch under normal pressure；The mass ratio of wherein phenolic resin and catalytic slurry is preferably 7:1 to 8:1, temperature
Preferably 130 DEG C to 135 DEG C of degree.
Crude phenols appearance in the application darkly brown liquid, wherein phenol quality percentage is about 39%, o-cresol quality
Percentage is about 9.3%, and paracresol mass percent is about 28.3%, and xylenol mass percent is about 12.4%, three cresols
Mass percent is about 1%, other material mass percentages are about 10%.
Condensation reaction：It is that a macromolecular is synthesized with covalently bonded after two or more organic molecules interact,
And it is often accompanied by the reaction for losing small molecule (such as water, hydrogen chloride, alcohol).
Polycondensation reaction mechanism
Catalytic slurry：Be refinery catalytic cracking unit discharge residue oil, property is unstable, wherein containing 30% to
50% or so saturated hydrocarbons, 40% to 60% aromatic hydrocarbons and polycyclic aromatic hydrocarbon and 10% resin and asphalt contain in slurry oil
1% catalyst dust.
Phenolic resin is divided into two class of thermosetting property and thermoplasticity, it is contemplated that asphalt modulation and requires heat to 130- using process
180 DEG C, thermosetting resin is not applicable, therefore the application selects and prepares thermoplastic phenolic resin.Subtract steaming dehydration as in pressure-
Heating dehydration is carried out under the conditions of 0.086Mpa.
Due to implementing above-mentioned technical proposal, the application, directly as raw material, reacts with formaldehyde using crude phenols and prepares phenolic aldehyde tree
Fat intermediate product, the process is without distilling cutting higher boiling aldehydes matter, and low energy consumption, and no waste generates, and avoids environmental pollution,
The phenolic resin precast is modulated with catalytic slurry again, prepares better than No. 200 road asphalt series of products.The application technique stream
Journey is short, and equipment is few, and low energy consumption, and pollution is few, while solving slurry oil technical indicator (i.e. softening point is less than 30 DEG C) and not reaching requirement
The problem of.
Description of the drawings
The concrete structure of the application is provided by drawings and examples below：
Fig. 1 is the process flow chart of the application.
Specific implementation mode
The application is not limited by following embodiments ,+
Specific embodiment can be determined according to the technical solution of the application and actual conditions.
Embodiment 1, as shown in Figure 1, crude phenols comprehensive utilization process includes the following steps：
Crude phenols and formalin are mixed to form the first mixture, wherein crude phenols and formaldehyde in formalin by the first step
Molar ratio is 1:0.75, the mass fraction of formaldehyde in formalin>35%；It is the first mixture gross mass that quality, which is added,
2%, a concentration of 10% aqueous hydrochloric acid solution carry out condensation reaction 1.5 hours, temperature is 70 DEG C, and pressure 0MPa is obtained small
The mixed aqueous solution of molecule condensation product；
The mixed aqueous solution of small molecule condensation product is carried out polycondensation reaction 5 hours by second step, and temperature is 90 DEG C, pressure 0MPa,
Obtain resin water mixed liquid；
Third walks, and resin water mixed liquid is dehydrated at 130 DEG C, -0.086MPA, obtains phenolic resin, the phenolic resin color
It is relatively deep, hard brittle solids under room temperature, average molecular weight 668,123 DEG C of softening point；
4th step, by phenolic resin and catalytic slurry with mass ratio 7：1, it is stirring uniformly to obtain modification under 140 DEG C of temperature, normal pressure
Pitch, (25 DEG C, 100g, 5s) of needle penetration are 208 (1/10mm), ductility (25 DEG C, be not less than) 21.9cm, 32 DEG C of softening point.
No. 200 road asphalts：Needle penetration (25 DEG C, 100g, 5s) (1/10mm) is 201-300, ductility (25 DEG C, be not less than)
(cm)-, softening point (DEG C) 30-45.Using the optimum process of embodiment 1 known to analysis, No. 200 road asphalts or performance can be made
Better than the modified pitch of No. 200 road asphalts.
Embodiment 2, crude phenols comprehensive utilization process include the following steps：
Crude phenols and formalin are mixed to form the first mixture, wherein crude phenols and formaldehyde in formalin by the first step
Molar ratio is 1:0.5, the mass fraction of formaldehyde in formalin>35%；It is the first mixture gross mass that quality, which is added,
0.3%, a concentration of 8% aqueous hydrochloric acid solution carry out condensation reaction 1 hour, temperature is 65 DEG C, and pressure is -0.05MPa, is obtained
The mixed aqueous solution of small molecule condensation product；
The mixed aqueous solution of small molecule condensation product is carried out polycondensation reaction 3 hours by second step, and temperature is 85 DEG C, and pressure is-
0.05MPa obtains resin water mixed liquid；
Third walk, resin water mixed liquid is dehydrated at 120 DEG C, -0.01MPA, obtains phenolic resin, the phenolic resin color compared with
It is shallow, there are mobility, average molecular weight 220, -13 DEG C of softening point under room temperature；
4th step, by phenolic resin and catalytic slurry with mass ratio 3：1, it is stirring uniformly to obtain modification under 95 DEG C of temperature, normal pressure
Pitch, (25 DEG C, 100g, 5s) of needle penetration are 840 (1/10mm), ductility (25 DEG C, be not less than)-cm, softening point-DEG C.
Embodiment 3, as shown in Figure 1, crude phenols comprehensive utilization process includes the following steps：
Crude phenols and formalin are mixed to form the first mixture, wherein crude phenols and formaldehyde in formalin by the first step
Molar ratio is 1:0.75, the mass fraction of formaldehyde in formalin>35%；It is the first mixture gross mass that quality, which is added,
2%, a concentration of 10% aqueous hydrochloric acid solution carry out condensation reaction 1.5 hours, temperature is 70 DEG C, and pressure 0MPa is obtained small
The mixed aqueous solution of molecule condensation product；
The mixed aqueous solution of small molecule condensation product is carried out polycondensation reaction 4 hours by second step, and temperature is 90 DEG C, pressure 0MPa,
Obtain resin water mixed liquid；
Third walks, and resin water mixed liquid is dehydrated at 110 DEG C, -0.086MPA, obtains phenolic resin, the phenolic resin color
It is relatively deep, hard brittle solids under room temperature, average molecular weight 572,92 DEG C of softening point；
4th step, by phenolic resin and catalytic slurry with mass ratio 8：1, it is stirring uniformly to obtain modification under 140 DEG C of temperature, normal pressure
Pitch, (25 DEG C, 100g, 5s) of needle penetration are 242 (1/10mm), ductility (25 DEG C, be not less than) 17.1cm, softening point-DEG C.
Embodiment 4, crude phenols comprehensive utilization process include the following steps：
Crude phenols and formalin are mixed to form the first mixture, wherein crude phenols and formaldehyde in formalin by the first step
Molar ratio is 1:2, the mass fraction of formaldehyde in formalin>35%；It is the 5% of the first mixture gross mass that quality, which is added,
, a concentration of 12% aqueous hydrochloric acid solution carry out condensation reaction 2 hours, temperature is 75 DEG C, and pressure 0.05MPa obtains small point
The mixed aqueous solution of sub- condensation product；
The mixed aqueous solution of small molecule condensation product is carried out polycondensation reaction 6 hours by second step, and temperature is 95 DEG C, and pressure is
0.05MPa obtains resin water mixed liquid；
Third walk, resin water mixed liquid is dehydrated at 160 DEG C, -0.1MPA, obtains phenolic resin, the phenolic resin color compared with
It is deep, hard brittle solids under room temperature, average molecular weight 763,107 DEG C of softening point；
4th step, by phenolic resin and catalytic slurry with mass ratio 9：1, it is stirring uniformly to obtain modification under 180 DEG C of temperature, normal pressure
Pitch, (25 DEG C, 100g, 5s) of needle penetration are 870 (1/10mm), ductility (25 DEG C, be not less than)-cm, softening point-DEG C.
For integrated embodiment 1 to embodiment 4, technological parameter is adjustable to allot a variety of modified pitch by changing, can be according to reality
It is prepared by demand.Technological process is short, easy to operate in the application；Without incineration of solid waste, environmental pollution is avoided, it is raw
Production modified pitch directly obtains economic recovery；Equipment needed for corresponding technique is few, and investment is small.
Embodiment 4, embodiment 5, embodiment 6 only carry out the preceding three step process in embodiment 1, and difference is listed in
Table 1.
By embodiment 1 and 1 comprehensive analysis of table：In the case of identical inventory, the reaction time gets over long molecule amount
It is bigger, but it is less than polycondensation reaction in 3 hours, the yield of thermoplastic phenolic resin is extremely low；Reaction more than six hours, system are held
Easily occur to gather cruelly, molecular weight sharply increases, and process is difficult to control, and is not suitable for producing and processing.
Embodiment 7 only carries out the preceding three step process in embodiment 1, and difference is listed in table 2 to embodiment 11.
By embodiment 1 and 2 comprehensive analysis of table：With the raising of dehydration temperaturre, the molecular weight of phenolic resin and soft
Change point all to increase, adjustable type is more during later stage reconciliation modified pitch；It is difficult but when temperature is more than 140 DEG C
To control constant temperature time.
Known to integrated embodiment 1 to embodiment 11：Reaction temperature is low, and initial reaction is slowly mild, and the reaction time is long, reaction
Temperature height is swift in response, and reacts too fast and is difficult to control；When concentration of hydrochloric acid is excessively high or dosage is big, reaction velocity of initiation is fast, occurs sudden and violent
It is poly-；Concentration is too low or dosage hour, reaction cannot carry out or cause overlong time.
The above technical characteristic constitutes embodiments herein, can basis with stronger adaptability and implementation result
Actual needs increases and decreases inessential technical characteristic, to meet the needs of different situations.
Table 1
Table 2
| Test number | Dehydration | Phenolic resin situation | Average molecular weight | Softening point |
| Embodiment 7 | 95 DEG C of temperature | Color is deeper, hard brittle solids under room temperature | 527 | 76℃ |
| Embodiment 8 | 105 DEG C of temperature | Color is deeper, hard brittle solids under room temperature | 563 | 85℃ |
| Embodiment 9 | 115 DEG C of temperature | Color is deeper, hard brittle solids under room temperature | 575 | 96℃ |
| Embodiment 10 | 125 DEG C of temperature | Color is deeper, hard brittle solids under room temperature | 603 | 112℃ |
| Embodiment 11 | 135 DEG C of temperature | Color is deeper, hard brittle solids under room temperature | 668 | 123℃ |
Claims (10)
1. a kind of crude phenols comprehensive utilization process, it is characterised in that include the following steps：
Crude phenols and formalin are mixed to form the first mixture by the first step, and it is small that aqueous hydrochloric acid solution progress condensation reaction 1 is added
Up to 2 hours, the mixed aqueous solution of small molecule condensation product is obtained；
The mixed aqueous solution of above-mentioned small molecule condensation product is carried out polycondensation reaction 3 to 6 hours by second step, obtains the mixing of resin water
Liquid；
Third walks, and is dehydrated above-mentioned resin water mixed liquid to obtain phenolic resin；
Above-mentioned phenolic resin and catalytic slurry are stirred to get modified pitch by the 4th step.
2. crude phenols comprehensive utilization process according to claim 1, it is characterised in that：Setting-up point in the first step is
65 DEG C to 75 DEG C, the polycondensation reaction temperature in second step is 85 DEG C to 95 DEG C, and the dehydration temperaturre in third step is 120 DEG C to 170
℃。
3. crude phenols comprehensive utilization process according to claim 2, it is characterised in that：Setting-up point in the first step is excellent
Be selected as 70 DEG C, the polycondensation reaction temperature in second step is preferably 90 DEG C, third step in dehydration temperature be preferably 130 DEG C extremely
135℃。
4. crude phenols comprehensive utilization process according to claim 1 or 2, it is characterised in that：Condensation reaction pressure in the first step
Power is -0.05MPa to 0.05MPa, and the polycondensation reaction pressure in second step is -0.05MPa to 0.05MPa, de- in third step
Water pressure is -0.01MPa to -0.1MPa.
5. crude phenols comprehensive utilization process according to claim 1 or 2, it is characterised in that：The hydrochloric acid water being added in the first step
Solution quality is the 0.2% to 5% of the first mixture gross mass, aqueous hydrochloric acid solution a concentration of 8% to 12%.
6. crude phenols comprehensive utilization process according to claim 5, it is characterised in that：The aqueous hydrochloric acid solution being added in the first step
It is preferably 2% that quality, which accounts for the first mixture gross mass percentage, and aqueous hydrochloric acid solution concentration is preferably 10%.
7. crude phenols comprehensive utilization process according to claim 1 or 2, it is characterised in that：Polycondensation reaction is anti-in second step
It is 5 hours between seasonable.
8. crude phenols comprehensive utilization process according to claim 1 or 2, it is characterised in that：Crude phenols in the first step and formaldehyde
The molar ratio of formaldehyde in aqueous solution is 1:0.4 to 1:2；Preferably 1:0.75.
9. crude phenols comprehensive utilization process according to claim 1 or 2, it is characterised in that：Formalin in the first step
The mass fraction of middle formaldehyde>35%.
10. crude phenols comprehensive utilization process according to claim 1 or 2, it is characterised in that：In 4th step phenolic resin with urge
Carburetion is starched with mass ratio 3:1 to 9:1, temperature is 95 DEG C to 180 DEG C, and modified pitch is uniformly mixing to obtain under normal pressure；Wherein phenolic aldehyde
The mass ratio of resin and catalytic slurry is preferably 7:1 to 8:1, temperature is preferably 130 DEG C to 135 DEG C.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711375797.3A CN108395667A (en) | 2017-12-19 | 2017-12-19 | Crude phenols comprehensive utilization process |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711375797.3A CN108395667A (en) | 2017-12-19 | 2017-12-19 | Crude phenols comprehensive utilization process |
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ID=63094376
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1631946A (en) * | 2004-11-10 | 2005-06-29 | 中国石油化工股份有限公司 | Thermosetting resin preparing method and use thereof |
| CN102532920A (en) * | 2010-12-17 | 2012-07-04 | 中国石油天然气股份有限公司 | Warm mixed asphalt cement and preparation method thereof |
| CN106496469A (en) * | 2016-11-09 | 2017-03-15 | 赵鹏瑞 | A kind of method for preparing phenolic resin as primary raw material with crude phenols |
-
2017
- 2017-12-19 CN CN201711375797.3A patent/CN108395667A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1631946A (en) * | 2004-11-10 | 2005-06-29 | 中国石油化工股份有限公司 | Thermosetting resin preparing method and use thereof |
| CN102532920A (en) * | 2010-12-17 | 2012-07-04 | 中国石油天然气股份有限公司 | Warm mixed asphalt cement and preparation method thereof |
| CN106496469A (en) * | 2016-11-09 | 2017-03-15 | 赵鹏瑞 | A kind of method for preparing phenolic resin as primary raw material with crude phenols |
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Application publication date: 20180814 |